You could build a pretty good team with the first-round picks the Maple Leafs have dealt away the past 20 years.

Of course, many other NHL teams could say the same. They have regretted the move for years, while others had no second thoughts about losing such assets, either because they needed the live bodies in return or have stockpiled enough picks that it was worth the risk.

Since the late 1980s, the Leafs have taken that plunge many times, but it has yet to pay off in Stanley Cup. As they seek to avoid an eighth straight year out of the playoffs, the players representing woulda-coulda-shoulda Leaf picks frequent the league.

Here a starting six comprised of the Leafs’ lost generation:

Goal

Roberto Luongo

Leaf connection: This pick was traded to the Islanders in 1997 when Leafs ownership started getting misty-eyed about Wendel Clark. Cliff Fletcher undid some of his good work in the Mats Sundin trade by packing Kenny Jonsson, Darby Hendrickson, junior Sean Haggerty and this first-rounder for Clark, Mathieu Schneider and D.J. Smith. The Isles took Luongo fourth overall.

Aftermath

The irony of the Leafs now being pressed by Vancouver to give up young talent to acquire Luongo is quite rich. But the Leafs did end up with stability in goal with Curtis Joseph and Ed Belfour, far more than the Isles, who squandered Luongo and ended up with Rick DiPietro.

Defence

Scott Niedermayer

Leaf connection: Opening the 1989-90 season with a 1-5 record and 37 goals against, GM Floyd Smith hit the panic button. He grabbed veteran defenceman Tom Kurvers, a member of the 1986 Cup champion Canadiens, from New Jersey. The price would not have to be paid until two years down the road when Smith obviously thought the Leafs would be higher in the standings.

But the team spent all of the 1990-91 sweating that Jersey would end up with Eric Lindros. The Leafs avoided the cellar, but lost on Niedermayer third overall.

Aftermath

The stability Niedermayer would have brought to the blueline, especially if the Leafs kept him in the deals that added Doug Gilmour and Mats Sundin, would’ve made the Leafs contenders throughout the ’90s. Instead, Niedermayer brought Cup magic to Jersey and Anaheim.

Defence

Darius Kasparaitis

Leaf connection: The Isles wanted to move up in the ’92 draft, while Fletcher didn’t want to fall too far and miss for a creative centre Brandon Convery. Toronto took the gamble Convery would still be there at eighth spot and also came away with feisty forward Grant Marshall. But neither made much impact, while the abrasive and colourful Lithuanian played close to 1,000 regular season and playoff games on defence.

Forward

Dainius Zubrus

Leaf connection: Toronto gave the Flyers a first- and second-rounder as part of the package for defenceman Dmitry Yushkevich from the Flyers. Missing a Kasparaitis-type player to keep foes honest crossing the blueline, the Leafs did well by Yushkevich for years. But long after he was forced to curtail his NHL career because of blood clots and later ended his playing days in the KHL, Zubrus is still going strong at age 34.

Aftermath

Since the Leafs moved back to the Eastern Conference in 1998, Zubrus has been a thorn in their side with Philly, Montreal, Washington and now, New Jersey.

Forward

Tyler Seguin

Leaf connection: The book on the Phil Kessel trade is far from closed. But Leafs scouts had to put on a brave face for TV at the 2010 draft when Boston called Seguin’s name second-overall after the team’s unexpected crash and burn. Kessel’s awkward exit from Boston and his discomfort in the Toronto spotlight contrasted with Seguin’s appeal as the Bruins were taking off.

Aftermath

With a Cup in his rookie year and 13 points in 12 starts against the Leafs, Seguin is money in the bank for Boston. That doesn’t mean the Leafs have done poorly by Kessel’s 99 goals to date, but they also gave up a second top-rounder that became defenceman Dougie Hamilton, who has also made the team.

Forward

Lars Eller

Leaf connection: GM John Ferguson’s attempt to improve goaltending and get some toughness in the lineup led to a big 2007 trade with San Jose for Vesa Toskala and winger Mark Bell. Ferguson had a strong scouting background and knew the pitfalls of Toronto giving up yet another high pick. But there was also pressure to make the playoffs. The Sharks moved the pick to the Blues who selected the big Danish-born forward.

Aftermath

A surprise inclusion in the 2010 trade with the Canadiens for goalie Jaroslav Halak, Eller had 28 points for the Habs last year in a two-way role. Not a huge loss for the Leafs, except that Toskala and Bell are long gone and Eller is playing for their historical and divisional playoff rivals.

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Maple Leafs' all-traded first-round all-stars

You could build a pretty good team with the first-round picks the Maple Leafs have dealt away the past 20 years.

Of course, many other NHL teams could say the same. They have regretted the move for years, while others had no second thoughts about losing such assets, either because they needed the live bodies in return or have stockpiled enough picks that it was worth the risk.

Since the late 1980s, the Leafs have taken that plunge many times, but it has yet to pay off in Stanley Cup. As they seek to avoid an eighth straight year out of the playoffs, the players representing woulda-coulda-shoulda Leaf picks frequent the league.